Home 7-(4-Fluorobenzylidene)-3-(4-fluorophenyl)-N-phenyl-3,3a,4,5,6,7-hexahydro-2H-indazole-2-carbothioamide–dimethylformamide (2/1), C27H23F2N3S, 0.5(C3H7NO)
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7-(4-Fluorobenzylidene)-3-(4-fluorophenyl)-N-phenyl-3,3a,4,5,6,7-hexahydro-2H-indazole-2-carbothioamide–dimethylformamide (2/1), C27H23F2N3S, 0.5(C3H7NO)

  • Obaid Fahad Aldosari , Bakr F. Abdel-Wahab , Mohammad Hayal Alotaibi , Amany S. Hegazy , Benson M. Kariuki EMAIL logo and Gamal A. El-Hiti ORCID logo EMAIL logo
Published/Copyright: August 17, 2019
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Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 234 Issue 6

Abstract

C27H23F2N3S, 0.5(C3H7NO), monoclinic, C2/c (no. 15), a = 25.1579(10) Å, b = 9.9356(4) Å, c = 20.1799(7) Å, β = 91.741(4)°, V = 5041.8(3) Å3, Z = 8, Rgt(F) = 0.0508, wRref(F2) = 0.1385, T = 296(2) K.

CCDC no.: 1920908

The molecular structure is shown in the figure. Table 1 contains crystallographic data and Table 2 contains the list of the atoms including atomic coordinates and displacement parameters.

Table 1:

Data collection and handling.

Crystal:Colourless needle
Size:0.52 × 0.31 × 0.11 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:0.17 mm−1
Diffractometer, scan mode:SuperNova, ω
θmax, completeness:29.9°, >99%
N(hkl)measured, N(hkl)unique, Rint:23341, 6338, 0.035
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 4290
N(param)refined:345
Programs:CrysAlisPRO [1], SHELX [2], [3], WinGX/ORTEP [4]
Table 2:

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2).

AtomxyzUiso*/Ueq
C10.92723(8)0.1198(3)0.69906(10)0.0697(6)
C20.93112(8)0.2553(3)0.70272(12)0.0826(7)
H20.9630430.2982240.6942120.099*
C30.88650(8)0.3296(2)0.71946(11)0.0707(6)
H30.8885620.4230010.7213730.085*
C40.83934(7)0.26626(18)0.73320(8)0.0496(4)
C50.83759(7)0.1282(2)0.72919(11)0.0642(5)
H50.8061400.0838140.7384690.077*
C60.88153(8)0.0535(2)0.71168(11)0.0729(6)
H60.879713−0.0397630.7086610.087*
C70.79256(7)0.34778(18)0.75499(8)0.0488(4)
H70.7980130.4426510.7437690.059*
C80.78232(7)0.33495(17)0.82986(8)0.0482(4)
H80.8027100.2582670.8475960.058*
C90.72445(7)0.30129(16)0.83089(8)0.0451(4)
C100.69490(7)0.30085(17)0.89248(8)0.0482(4)
C110.71386(8)0.40701(19)0.94150(9)0.0594(5)
H11A0.7038030.3802080.9856070.071*
H11B0.6959190.4911120.9310240.071*
C120.77351(8)0.4304(2)0.94189(9)0.0672(5)
H12A0.7914000.3519260.9604740.081*
H12B0.7821370.5065590.9703090.081*
C130.79426(8)0.4573(2)0.87305(9)0.0618(5)
H13A0.7770770.5363150.8540160.074*
H13B0.8322890.4734630.8757750.074*
C140.72320(7)0.33496(17)0.66250(8)0.0486(4)
C150.63994(7)0.32426(17)0.59232(8)0.0477(4)
C160.65760(7)0.29135(18)0.53006(8)0.0538(4)
H160.6924160.2626830.5248760.065*
C170.62300(8)0.30144(19)0.47552(9)0.0599(5)
H170.6349090.2803240.4335960.072*
C180.57145(9)0.3422(2)0.48264(10)0.0663(5)
H180.5485040.3476880.4457330.080*
C190.55367(8)0.3748(2)0.54429(11)0.0674(5)
H190.5185980.4016250.5492650.081*
C200.58811(7)0.3677(2)0.59897(9)0.0579(4)
H200.5763290.3922570.6405000.070*
C210.65562(7)0.21164(18)0.89975(8)0.0514(4)
H210.6497260.1541490.8639120.062*
C220.62046(7)0.19049(18)0.95540(9)0.0530(4)
C230.60158(7)0.0611(2)0.96603(10)0.0612(5)
H230.609984−0.0067930.9364190.073*
C240.57063(8)0.0307(2)1.01942(11)0.0741(6)
H240.558494−0.0564401.0263490.089*
C250.55852(9)0.1322(3)1.06145(12)0.0772(6)
C260.57458(9)0.2611(2)1.05289(12)0.0783(6)
H260.5649400.3281701.0823670.094*
C270.60562(8)0.2909(2)0.99935(11)0.0667(5)
H270.6167050.3790360.9926200.080*
N10.74100(5)0.30100(14)0.72527(6)0.0477(3)
N20.70220(5)0.28201(14)0.77347(6)0.0477(3)
N30.67126(6)0.30801(16)0.65128(7)0.0529(4)
H3A0.6547790.2764860.6846140.063*
S10.76395(2)0.40457(7)0.60911(2)0.0751(2)
F10.97061(5)0.04890(18)0.68091(7)0.1032(5)
F20.52817(7)0.10352(17)1.11445(9)0.1232(6)
C28a0.5459(3)0.1446(7)0.7054(3)0.1081(19)
H28a0.5351660.1306590.6614170.130*
C29a0.5241(3)0.1818(9)0.8189(3)0.120(2)
H29Aa0.5257800.2753150.8306220.180*
H29Ba0.5587540.1422670.8244130.180*
H29Ca0.4997210.1363740.8469790.180*
C30a0.4526(3)0.1886(10)0.7310(5)0.154(4)
H30Aa0.4511600.2103820.6846070.230*
H30Ba0.4375350.2609540.7556920.230*
H30Ca0.4328080.1075900.7382320.230*
N4a0.5064(7)0.1690(4)0.7523(8)0.091(2)
O1a0.59251(18)0.1408(6)0.7192(3)0.1327(18)

  1. aOccupancy: 0.5.

Source of material

The title compound was synthesized from reaction of equimolar quantities of 7-(4-fluorobenzylidene)-3-(4-fluorophenyl)-3,3a,4,5,6,7-hexahydro-2H-indazole and phenyl isothiocyanate in anhydrous ethanol under reflux for 2 h. The crude product was collected by filtration, washed with ethanol and recrystallized from dimethylformamide to give the title compound in 82% yield as colourless crystals (Mp. 228–230 °C).

Experimental details

All hydrogen atoms were placed in calculated positions and refined using a riding model. The N—H bond was fixed at 0.86 Å (AFIX 43 instruction in SHELXL [2], [3]), with displacement parameters set to 1.2 times Ueq(N). C—H distances for sp2 carbon atoms were set to 0.93 Å (AFIX 43) and Uiso(H) set to 1.2 times Ueq(C). The methine C—H distance was set to 0.98 Å (AFIX 13) and Uiso(H) set to 1.2 times Ueq(C). The methylene C—H distances was set to 0.97 Å (AFIX 23) and Uiso(H) set to 1.2 times Ueq(C). Methyl C—H distances were set to 0.96 Å and Uiso(H) set to 1.5 times Ueq(C) with the group allowed to rotate about the C—C bond (AFIX 137). The dimethylformamide molecule lies on a two-fold rotation axis and was refined with restrained geometry and displacement parameters (DFIX, SIMU).

Comment

Pyrazole containing compounds are an essential core scaffold in many natural products and show various biological activities [5], [6], [7]. Several synthetic pathways have been reported for the synthesis of pyrazoles [8], [9], [10].

The asymmetric unit consists of one molecule of the title compound and half a molecule of dimethyl formamide solvent located on a two-fold rotation axis (see the figure). Geometric parameters are all in the expected ranges [11]. The molecule consists of two fluorophenyl groups [A (F1, C1—C6) and D (F2, C22—C26)], a hexahydroindazolyl group [B (N1, N2, C7—C13)] and a phenyl group [C (C15–C20)]. The cyclohexane segment (C8—C13) of B is in chair conformation. The pyrazolyl ring of B assumes an envelop conformation although it is nearly planer with the flap (C7) deviating by only 0.132(3) Å from the plane of the rest of the ring (C8, C9, N1, N2). An intramolecular contact is observed (N3—H3A⋯N2) and the same hydrogen atom also interacts with the DMF solvent molecule (N3—H3A⋯O1). C—H⋯F and C—H⋯S interactions form an extended network in the crystal structure. Edge-to-face interaction occurs between the phenyl (C) and fluorophenyl (D) rings with a centroid-to-centroid distance of 5.1 Å.

Acknowledgements

The authors would like to thank the Deanship of Scientific Research at Majmaah University for supporting this work under Project Number No. 1440-127, and to Cardiff University for continued support.

References

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Received: 2019-04-09
Accepted: 2019-06-05
Published Online: 2019-08-17
Published in Print: 2019-11-26

©2019 Obaid Fahad Aldosari et al., published by De Gruyter, Berlin/Boston

This work is licensed under the Creative Commons Attribution 4.0 Public License.

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  1. Frontmatter
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  3. Crystal structure of ethyl 3-(4-methoxyphenyl)-5-methylcarbamoyl-1H-pyrazole-4-carboxylate, C15H17N3O4
  4. 7-(4-Fluorobenzylidene)-3-(4-fluorophenyl)-N-phenyl-3,3a,4,5,6,7-hexahydro-2H-indazole-2-carbothioamide–dimethylformamide (2/1), C27H23F2N3S, 0.5(C3H7NO)
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  63. Crystal structure of (N-n-butyl, N-methyl-dithiocarbamato-κ2 S,S′)-chlorido-dimethyl-tin(IV), C8H18ClNS2Sn
  64. Crystal structure of (2,2′-bipyridyl)bis(4-bromobenzyl)dibromidotin(IV), C24H20Br4N2Sn
  65. Crystal structure of (2,2′-bipyridyl)bis(4-chlorobenzyl)dichloridotin(IV), C24H20Cl4N2Sn
  66. Crystal structure of N-methyl-N-phenyl(methylsulfanyl)carbothioamide, C9H11NS2
  67. Crystal structure of 4-phenylpiperazin-1-ium (4-phenylpiperazin-1-yl)carbothioylsulfanide, [C10H15N2][C11H13N2S2]
  68. Crystal structure of catena-{di-aqua-sodium [n-butyl(methyl)carbamothioyl]sulfanide}n, [C6H16NNaO2S2]n
  69. Crystal structure of (2-([1,1-bis(hydroxymethyl)-2-oxyethyl]iminomethyl)-5-(n-decyl)phenolato)-dimethyl-tin(IV), C23H39NO5Sn
  70. Crystal structure of 4-chloro-N′-[(1E)-(3-ethoxy-2-hydroxyphenyl)methylidene]benzohydrazide – a Z′ = 3 structure, C16H15ClN2O3
https://doi.org/10.1515/ncrs-2019-0261
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Articles in the same Issue

  1. Frontmatter
  2. Crystal structure of [aqua[2,2′-(1,2-phenylene)bis(1H-imidazole-4-carboxylato-5-carboxy)-κ4N3,N3′,O4,O4′] zinc(II)] monohydrate, C16H10N4O9Zn⋅H2O
  3. Crystal structure of ethyl 3-(4-methoxyphenyl)-5-methylcarbamoyl-1H-pyrazole-4-carboxylate, C15H17N3O4
  4. 7-(4-Fluorobenzylidene)-3-(4-fluorophenyl)-N-phenyl-3,3a,4,5,6,7-hexahydro-2H-indazole-2-carbothioamide–dimethylformamide (2/1), C27H23F2N3S, 0.5(C3H7NO)
  5. Crystal structure of 4,4′-(hydrazonomethylene)diphenol dihydrate, C13H16N2O4
  6. Crystal structure of 4-methoxyphenyl-3-phenylpropiolate, C16H12O3
  7. Crystal Structure of tris(tetrakis{1-vinyl-1H-imidazole-κN}copper(II)) bis[tri-μ2-bromido-tetrabromido-bis(1-vinyl-1H-imidazole-κN)tetracopper(I)], C80H96N32Cu11Br14
  8. Crystal structure of (E)-2-(3,6-bis(diethylamino)-9H-xanthen-9-yl)-N′-(quinoxalin-2-ylmethylene)benzohydrazide, C37H36N6O2
  9. Crystal structure of 4-(1-phenylimidazo[1,5-a]pyridin-3-yl)benzoic acid (C20H14N2O2)
  10. Crystal structure of 3-fluoro-3-methyl-1-((2-nitrophenyl)sulfonyl)-5,5-diphenylpiperidine, C24H23FN2O4S
  11. Crystal structure of dimethyl 3,12-dibenzyl-6,10-diphenyl-3,12-diazapentacyclo [6.3.1.02.7.04.11.05.9]-dodecane-7,11-dicarboxylate — acetone (2/1), C40H38N2O2 ⋅ 0.5C3H6O
  12. Crystal structure of poly[(μ2-2-(1H-1,2,4-triazol-1-yl)benzoato-κ4O:O′:N:N′)silver(I)] monohydrate, C9H8AgO3N3
  13. Crystal structure of poly[(μ2-9H-carbazole-3,6-dicarboxylate-κ4O1,O2:O3,O4)(μ2-1,3-di(pyridin-4-yl)propane-κ2N:N′)cadmium(II)]monohydrate, C27H23N3O5Cd
  14. The synthesis and crystal structure of bis(2-(benzo[d]thiazol-2-yl)-5-methylbenzen-1-ido-κ2C,N)-(N,N′-diethyldithiocarbamato-κ2S,S′)iridium(III), C33H30N3S4Ir
  15. The crystal structure of 5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-(trifluoromethylsulfonyl)-1H-pyrazole-3-carboxamide, C12H6N4Cl2F6O3S
  16. Synthesis and crystal structure of poly[(μ2-nitrato-κ4O,O′:O′,O′′)-nitrato-κO-(μ2-1,4-bis((1H-imidazol-1-yl)methyl)benzene-κ2N:N′)cadmium(II)], C14H14N6O6Cd
  17. Crystal structure of ethyl (Z)-(4-oxo-4-phenylbut-2-en-2-yl)glycinate, C14H17NO3
  18. Halogen bonds in the crystal structure of 5-bromo-3,4′-bipyridine – 1,4-diiodotetrafluorobenzene (2/1), C26H14Br2F4I2N4
  19. Crystal structure of bis(2,2′-bipyridine-κ2N,N′)-tetrakis(μ2-3-(phenylsulfonamido)propanoato-κ2O:O′)-bis(3-(phenylsulfonamido)propanoato-κ2O,O′)digadolinium(III) – 2,2′-bipyridine (1/1), C84H84Gd2N12O24S6
  20. Crystal structure of poly[aqua(μ2-2-amino-1,4-benzenedisulfonato-κ2O:O′)bis(μ2-pyrazin-κ2N:N′)silver(I)], C14H16Ag2N5O8S2
  21. The crystal structure of 1,6-di-tert-butyl-1,1,3,3,4,4,6,6-octamethyl-2,2,5,5-tetrakis (trimethylsilyl)hexasilane, C28H78Si10
  22. Crystal structure of discandium triruthenium tetrasilicide, Sc2Ru3Si4
  23. Crystal structure of poly[(μ2-4-amino-1,5-naphthalenedisulfonato-κ4O,N:O′, N′)bis(μ2-hexamethylenetetramino-κ2N;N′)silver(I)], {C22H30Ag2N9O6S2}n
  24. Crystal structure of diaqua[5,5′-dicarboxy-2,2′-(propane-1,3-diyl)bis(1H-imidazole-4-carboxylato-κ4O,O′,N,N′)]zinc(II) dihydrate, C13H18N4O12Zn
  25. The crystal structure of poly [(μ3-N1,N4-bis(pyridin-3-yl)cyclohexane-1,4-dicarboxamide-κ3-O:N:N′)-(p-toluenesulfonato-κ2O,O′)silver(I)], C25H27Ag1N4O5S
  26. The crystal structure of 1,2-bis(3-bromophenoxy) ethane, C14H12Br2O2
  27. The crystal structure of 4-(pyren-1-yl)butyl-3-nitrobenzoate, C27H21NO4
  28. Crystal structure of bis[(2-(4-chlorophenyl)-5-methyl-1,3-dioxane-5-carboxylato-κ1O) (5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane-κ4N,N′,N′′,N′′′)]nickel(II), C40H60Cl2N4NiO8
  29. The crystal structure of 1,5-dinitro-2,3,4-trichlorobenzene, C6H1Cl3N2O4
  30. The crystal structure of the solid solution of 3,5-dinitropyrazole and 4-chlorine-3,5-dinitropyrazole, C3H1.24Cl0.76N4O4
  31. The cocrystal structure of 4-nitropyrazole — acetic acid (1/1), C5H7N3O4
  32. The crystal structure of propan-2-one O-(2,4,6-trinitrophenyl) oxime, C9H8N4O7
  33. The crystal structure of ethyl 2-(3-(2-ethoxy-2-oxoethyl)benzo[d] thiazol-2(3H)-ylidene)acetate, C15H17NO4S
  34. Crystal structure of (acetic acid-κ1O)-bis(μ2-2-chlorobenzoato-κ2O:O′)-(2-chlorobenzoato-κ1O)-(μ2-hydroxy-κ2O:O)-bis(1,10-phenanthroline-κ2N,N′)dimanganese(II) — methanol (1/1), C48H37Cl3Mn2N4O10
  35. Crystal structure of 3-methyl-2-phenyl-1,8-naphthyridine, C15H12N2
  36. Crystal structure of chlorido-(5-acetyl-2-(5-methylpyridin-2-yl)benzen-1-ido-κ2C,N)-pyridine-κN-palladium(II), C19H17ClN2OPd
  37. Crystal structure of (4-methyl-benzoato-κ2O,O′)-(5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane-κ4N,N′,N′′,N′′′)nickel(II) perchlorate monohydrate, C24H45ClN4NiO7
  38. Crystal structure of (1,4,7,10,13,16-hexaoxacyclooctadecane-κ6O6) 1,2,3,4,5-pentamethyl-cyclopenta-2,4-dien-1-yl(potassium, rubidium) — ammonia (1/2), [K0.3Rb0.7(18-crown-6)]Cp*⋅2 NH3, C22H45K0.3N2O6Rb0.7
  39. Crystal structure of (3E,5E)-1-((4-fluorophenyl)sulfonyl)-3,5-bis(3-nitrobenzylidene)piperidin-4-one — dichloromethane (2/1), C51H38Cl2F2N6O14S2
  40. Crystal structure of (E)-N′-((1,6-dihydropyren-1-yl)methylene)isonicotinohydrazide — methanol (1/1), C24H19N3O2
  41. Crystal structure of poly[aqua(μ2-2-amino-1,4-benzenedisulfonato-κ3N,O:O′)-(μ4-hexamethylenetetramino-κ4N:N′:N′′:N′′′)disilver(I)] monohydrate, C12H21Ag2N5O8S2
  42. Crystal structure of bis(acridin-10-ium) 2,5-dihydroxyterephthalate — 2,5-dihydroxyterephthalic acid (1/1), C21H15NO6
  43. The crystal structure of 1,12-diazaperylene, C18H10N2
  44. Crystal structure of 1-(5-(4-chlorophenyl)-3-(2-fluorophenyl)-4,5-dihydro-1H-pyrazol-1-yl)ethan-1-one, C17H14N2OFCl
  45. Crystal structure of (4aR,6aR,6bR,10S,12aR)-10-acetoxy-1,2,3,4, 4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a, 12b,13,14b-icosahydro-2,2,4a,6b,9,9,12a-heptamethylpicene-6a-carboxylic acid, C32H50O4
  46. The crystal structure of tetrachlorido-bis{1,3-bis(2,6-diisopropylphenyl)-1H-3λ4-imidazol-2-yl}-(μ2-pyrimidine-κ2N:N′)dipalladium(IV) — dichloromethane (1/2), C60H80Cl8N6Pd2
  47. The crystal structure of (E)-4-(7-methoxy-2-oxo-2H-chromen-8-yl)-2-methylbut-2-en-1-yl 4-nitrobenzoate, C22H19NO7
  48. Crystal structure of 3-methyl-N-(pyrimidin-5-ylmethyl)pyridin-2-amine, C11H12N4
  49. The crystal structure of 2,5-dichloroterephthalic acid dihydrate, C8H8Cl2O6
  50. The crystal structure of 2,4,6-tris[4-(1H-imidazol-1-yl)phenyl]-1,3,5-triazine — dimethylformamide (1/1), C33H28N10O
  51. Crystal structure of N-(adamantan-1-yl)-5-(dimethylamino)naphthalene-1-sulfonamide, C22H28N2O2S
  52. Crystal structure of poly[diaqua-(μ4-4-(3,5-dicarboxy-κ1O-phenoxy)phthalato-κ3O:O′:O′)cadmium(II)], C16H12CdO11
  53. Crystal structure of poly[diaqua-bis(μ2-3-((1H-imidazol-1-yl)methyl)benzoato-κ2N:O)manganese(II)], C22H22MnN4O6
  54. Crystal structure of 9-(3-phenoxyphenyl)-3,4,6,7,9,10-hexahydroacridine-1,8(2H,5H)-dione, C25H23NO3
  55. The crystal structure of poly[(μ3-2,4,6-tris[4-(1H-imidazol-1-yl)phenyl]-1,3,5-triazine-k3N:N′:N′′)-(nitrato-k2O,O)-(nitrato-k1O)zinc(II)] - N,N-dimethylacetamide (1/2), C38H39N13O8Zn
  56. Crystal structure of poly[(μ7-4-(3,5-dicarboxylatophenoxy)phthalato)-(1,10-phenanthroline-κ2N,N′)dizinc(II)], C28H14N2O9Zn2
  57. The crystal structure of methyl 2-(benzylamino)-5-(benzyloxy)benzoate, C22H21NO3
  58. Crystal structure of (1,4,8,11-tetraazacyclotetradecane)palladium(II) tetracyanoplatinate(II), C14H24N8PdPt
  59. Crystal structure of (pyridine-2-carboxylato-κ2N,O)-[2-(2-pyridyl)phenyl-κ2N,C1]palladium(II), C17H12N2O2Pd
  60. Crystal structure of (cyclohexane-1,4-diammonium) 4-[(4-carboxylatophenyl)disulfanyl]benzoate dimethylsulphoxide hydrate (1/1/1/1), [C6H16N2]2+[C14H8O4S2]2−⋅C2H6OS⋅H2O
  61. Crystal structure of the 2:1 co-crystal 2-[(2-carboxyphenyl)disulfanyl]benzoic acid – 3-bromobenzoic acid, 2(C14H10O4S2)⋅C7H5BrO2
  62. Crystal structure of chlorido-dimethyl-(phenylpiperazine-1-carbodithioato-κ2S,S′)tin(IV), C13H19ClN2S2Sn
  63. Crystal structure of (N-n-butyl, N-methyl-dithiocarbamato-κ2 S,S′)-chlorido-dimethyl-tin(IV), C8H18ClNS2Sn
  64. Crystal structure of (2,2′-bipyridyl)bis(4-bromobenzyl)dibromidotin(IV), C24H20Br4N2Sn
  65. Crystal structure of (2,2′-bipyridyl)bis(4-chlorobenzyl)dichloridotin(IV), C24H20Cl4N2Sn
  66. Crystal structure of N-methyl-N-phenyl(methylsulfanyl)carbothioamide, C9H11NS2
  67. Crystal structure of 4-phenylpiperazin-1-ium (4-phenylpiperazin-1-yl)carbothioylsulfanide, [C10H15N2][C11H13N2S2]
  68. Crystal structure of catena-{di-aqua-sodium [n-butyl(methyl)carbamothioyl]sulfanide}n, [C6H16NNaO2S2]n
  69. Crystal structure of (2-([1,1-bis(hydroxymethyl)-2-oxyethyl]iminomethyl)-5-(n-decyl)phenolato)-dimethyl-tin(IV), C23H39NO5Sn
  70. Crystal structure of 4-chloro-N′-[(1E)-(3-ethoxy-2-hydroxyphenyl)methylidene]benzohydrazide – a Z′ = 3 structure, C16H15ClN2O3
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